(4R,4aS,4'R,4a'S,6aR,6a'R,8R,8'R,9S,9'S,11aR,11bS,11a'R,11b'S)-8,8'-(decanedioylbis(oxy))bis(4,9,11b-trimethyltetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid) | 936133-70-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4R,4aS,4'R,4a'S,6aR,6a'R,8R,8'R,9S,9'S,11aR,11bS,11a'R,11b'S)-8,8'-(decanedioylbis(oxy))bis(4,9,11b-trimethyltetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid)
• CAS: 936133-70-9
• 化学式: C₅₀H₇₈O₈
• 分子量: 807.165
• InChiKey: FAGPSBNGKUUZJL-AYRBEICOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.71
• 重原子数：
  58.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  127.2
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,4aS,4'R,4a'S,6aR,6a'R,8R,8'R,9S,9'S,11aR,11bS,11a'R,11b'S)-8,8'-(decanedioylbis(oxy))bis(4,9,11b-trimethyltetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid) 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 bis((4R,4aS,6aR,8R,9S,11aR,11bS)-4-((3-hydroxypropoxy)carbonyl)-4,9,11b-trimethyltetradecahydro-6a,9-methanocyclohepta[a]naphthalen-8-yl) decanedioate
  参考文献：
  名称：

  New malonate macrocycle bearing two isosteviol moieties and its adduct with fullerene C60

  摘要：

  Macrocycle having two isosteviol moieties and malonate fragment has been synthesised, and its ability to inhibit the growth of Mycobacterium tuberculosis H37Rv in vitro with MIC value of 1 mu g cm(-3) has been demonstrated. The macrocycle adds fullerene C-60 at the activated methylene group to furnish the corresponding methanofullerene conjugate.

  DOI：

  10.1016/j.mencom.2011.04.006
• 作为产物：
  描述：

  异甜菊醇 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (4R,4aS,4'R,4a'S,6aR,6a'R,8R,8'R,9S,9'S,11aR,11bS,11a'R,11b'S)-8,8'-(decanedioylbis(oxy))bis(4,9,11b-trimethyltetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid)
  参考文献：
  名称：

  包含葡糖胺和二萜类异osteviol的第一大环糖萜类化合物的合成和抗结核活性。

  摘要：

  合成了包含葡糖胺和二萜类异戊烯醇部分的第一大环糖类萜，并评估了其对结核分枝杆菌H37Rv的抑制活性。

  DOI：

  10.1016/j.carres.2016.05.007

文献信息

• Open-Chain and Macrocyclic Polyethyleneglycol Esters of the Diterpenoid Isosteviol
  作者：I. Yu. Strobykina、M. G. Belenok、B. F. Garifullin、V. M. Babaev、V. E. Kataev

  DOI：10.1007/s10600-014-0987-8

  日期：2014.7

  Open-chain and macrocyclic derivatives of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) in which two isosteviol molecules were connected by polyethyleneglycol spacers were synthesized for the first time.

  首次合成了二萜类异雌二醇（16-氧代-ent-beyeran-19-酸）的开链和大环衍生物，其中两个异雌二醇分子由聚乙二醇间隔物连接。
• Synthesis of macrocycles on the basis of diterpenoid isosteviol and trehalose
  作者：B. F. Garifullin、R. R. Sharipova、I. Yu. Strobykina、O. V. Andreeva、M. A. Kravchenko、V. E. Kataev

  DOI：10.1134/s1070428015100231

  日期：2015.10

  Macrocyclic glycoterpenoids containing trehalose and isosteviol fragments have been synthesized. Selective screening has revealed compounds exhibiting antitubercular activity against H37RV, M. Avium and M. Terrae at a level comparable to the known antitubercular drugs isoniazid, ofloxacin, and pyrazinamide.
• Synthetic glycosides containing two isosteviol fragments functionalized with D-glucopyranose
  作者：B. F. Garifullin、R. R. Sharipova、I. Yu. Strobykina、V. M. Babaev、V. E. Kataev

  DOI：10.1134/s107042801404006x

  日期：2014.4

  The synthesis of isosteviol (16-oxo-ent-beyeran-19-oic acid) glycosides in which two isosteviol fragments functionalized with tetra-O-acetyl-D-glucopyranose are linked through a diester spacer is described for the first time.
• Development of synthetic approaches to macrocyclic glycoterpenoids on the basis of glucuronic acid and diterpenoid isosteviol
  作者：O. V. Andreeva、R. R. Sharipova、I. Yu. Strobykina、M. A. Kravchenko、A. S. Strobykina、A. D. Voloshina、R. Z. Musin、V. E. Kataeva

  DOI：10.1134/s1070428015090201

  日期：2015.9

  An approach has been developed to the synthesis of macrocyclic glycoterpenoids containing diterpenoid isosteviol and glucuronic acid fragments. Selective screening revealed compounds exhibiting antitubercular activity against H37RV, M. Avium, and M. Terrae strains at a level comparable to the known antitubercular drugs isoniazid, ofloxacin, and pyrazinamide. The compound possessing the highest antitubercular activity is non-cytotoxic toward human erythrocytes.